Transition metal-free controlled synthesis of bis[(trifluoromethyl)sulfonyl]ethyl-decorated heterocycles‡
Literature Information
Publication Date
2018-09-20
DOI
10.1039/C8QO00955D
Impact Factor
5.281
Authors
Pedro Almendros, Hikaru Yanai, Shoki Hoshikawa, Cristina Aragoncillo, Carlos Lázaro-Milla, Mireia Toledano-Pinedo, Takashi Matsumoto, Benito Alcaide
View Original
Abstract
Several heterocycles reacted with shelf-stable 2-(2-fluoropyridinium-1-yl)-1,1-bis[(trifluoromethyl)sulfonyl] ethan-1-ide, a latent Tf2CCH2 source, to give rise in a mild and controllable way to adducts via direct C–H bis[(trifluoromethyl)sulfonyl]ethylation reactions. This metal- and irradiation-free protocol is convenient. Besides, the volatile side-product 2-fluoropyridine can be smoothly eliminated under vacuum, which facilitates purification. The substrate scope survey discloses that exquisite chemo- and regioselectivities are achieved in a variety of heterocyclic systems. Of particular interest are the late-stage structural modification of known pharmaceuticals, such as the marketed drugs Phenazone (Antipyrine) and Edaravone, and the development of a water soluble fluorescent dye.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
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(3S,4aS,8aS)-2-[(2R,3S)-3-Amino-2-hydroxy-4-phenylbutyl]-N-(2-methyl-2-propanyl)decahydro-3-isoquinolinecarboxamide
CAS Number:
136522-17-3
Molecular Formula:
C24H39N3O2
(1-(2-(Dimethylamino)ethyl)-1H-pyrazol-4-yl)boronic acid
CAS Number:
1086063-73-1
Molecular Formula:
C7H14BN3O2
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